21. Sandy Weill

Banker and Wall Street dealmaker

"Learn how to be a loser, because it's important to be a loser to be a winner."

Financier and philanthropist, former chairman and CEO, CitigroupBorn: March 16, 1933, New York CityEducation: Bachelor's in government, Cornell University

Sandy Weill was arguably the financial industry's master dealmaker of his time. His triumph was to have built two financial services empires like no others at the time—one, Shearson, a giant; the other, Citigroup, a colossus. His tragedy is that both would be brought low as he watched from afar.

Citigroup was intended to be the crowning accomplishment of Weill's half-century of dealmaking on Wall Street. Through mergers and acquisitions, he built the first financial supermarket since the Depression-era Glass-Steagall Act walled off banks from other financial institutions, such as securities firms and insurers. At the heart of his creation was America's largest bank.

Sandy Weill defines the art of the Wall Street deal

Assembled two of Wall Street's great financial conglomerates, Shearson and Citigroup, shattering Glass-Steagall on the way, but would see both crumble.

The global financial crisis of 2008 unmasked Citigroup as an unmanageable—or, as Weill would later accuse his successors, unmanaged—corporation, devoid of the business synergies his dealmaking was meant to have enabled, and incapable of integrating its global businesses or of keeping tabs on risky investments and the staff making them.

Citi's stock fell from a high of $55 a share in 2007 to about $1 in 2009. The U.S. government stepped in with a $45 billion taxpayer bailout, and the company set about disassembling what Weill had built.

He retired as chairman of Citi in 2006, and the subprime mortgage market collapsed late in the summer of 2007. He had stepped down as CEO in 2003 in a wave of managerial restructuring that followed the stock market slump of 2002. Weill still owned 16 million shares of Citi stock, though, and tried to return in 2007 when CEO Chuck Prince, who had let its balance sheet balloon, resigned.

It might have been different had Weill not fallen out with his protégé Jamie Dimon, who as CEO of JPMorgan Chase found the synergies and management controls that eluded Citi, and steered it relatively unscathed through the financial crisis. Their 15-year partnership had ended in 1999, with Dimon being shown the door.

A falling out between Weill, then CEO of American Express, and Chairman James Robinson III in 1985 had set Weill and the young Dimon on the road to building Citi. Weill bought Commercial Credit, the troubled consumer finance arm of Control Data, for $7 million, and then began absorbing a blue-chip roster of Wall Street names: Shearson, Smith Barney and Salomon. The final piece was a $76 billion merger with Travelers Group, which closed in 1998.

Weill had been a dealmaker for a long time by then, having turned a small brokerage firm he co-founded in 1960, Carter Berlind Potoma & Weill, into Shearson Loeb Rhoades. Shearson was the second-largest securities firm on Wall Street, behind Merrill Lynch, when he sold it to American Express in 1981 for $930 million.

Though Weill became the company's president, the 1984 acquisition of investment bank Lehman Brothers quashed his ambition of becoming CEO. Lehman's Lewis Glucksman eventually got the job, and Weill was gone within a year. As it happened, he got Shearson back when AmEx began to dismantle in the early 1990s.

Speaking in 2012, Weill surprised everyone when he called for the breakup of big banks and the return of Glass-Steagall, given how aggressively he had lobbied for its repeal when creating Citi, enlisting former President Gerald Ford and former Treasury Secretary Robert Rubin to the cause. Last year he qualified his statements, saying that big banks could remain intact if "the right regulation" were in place and that they should only split up if they see it as in their own best interest.

Now in his 80s, Weill and his wife of more than 50 years, Joan, split their time between a vineyard home in Sonoma, Calif., which they bought in 2010, and their native New York. The couple are active philanthropists and fundraisers, including for Weill's alma mater, Cornell, and for Carnegie Hall.